I'm a novice to flight planning in general, most of the routes I use are either auto generated, or taken from rw sources, and I was wondering where I could go to start learning about real world flight planning, and what all this tons of stuff means?

Pick up a copy of Jeppesen's Instrument/Commercial Manual.

 

http://www.mypilotstore.com/mypilotstore/sep/1270

 

Or get your hands on a copy of the FAA's Instrument Flying Handbook.

 

http://www.faa.gov/regulations_policies/handbooks_manuals/aviation/

 

Both are great intros.